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Portnoy's Complaint by Philip Roth.

This well-known novel, once-controversial because of its graphic sexual and religious content, is the story of Alexander Portnoy, a profoundly troubled young Jewish man struggling with several disquieting obsessions. Narrated from a passionate, highly articulate and frantic stream of consciousness point of view, the book explores themes relating to the nature and purpose of sexuality, Jewishness, and freedom.

This narrative of one man's tortured explorations of his past and present is told from the first person point of view, unfolding through a complicated, cause-triggering-effect relationship between past and present, idea and feeling, insight and observation. It begins with the narrator's blunt, serio-comic description of his very Jewish, very controlling, and very frustrating parents, and continues with a graphic and uncompromising description of his obsession with sex in general, and masturbation in particular.

Narration reveals that the teller of these often raucous, frequently ranting, occasionally poignant stories, Alex Portnoy, is in his early thirties, Jewish, highly sexed, and working in what he sees as a successful public life. His contentment with that life, however, is as he describes it seriously undermined by his fear that his sexually rapacious private life is going to be exposed. That private life, he says (as he speaks to his silent psychiatrist), is focused on sex with shikses—with non-Jewish girls that are, according to the orthodoxy of his conservative Jewish faith, forbidden, which in Alex's mind makes them all that more appealing.

As he recounts his stories of humiliation at the hands of his parents, his increasingly desperate adult relationships with women and his increasingly desperate childhood relationships with girls, Alex's long-suppressed feelings erupt in almost orgasmic explosions of rage, frustration, fear ... and eventually loneliness. His resentments of his Jewish-ness, of his parents' controlling natures and failures, and of his failure to feel at home in the freedom-inspiring America of his dreams all, throughout the course of both his life and the narrative of that life, surge to the surface of his psyche.

Specific memories of specific women form key narrative anchors in the midst of the surging emotion and memory. There is: The Monkey, the non-Jewish Southern girl whose nickname comes from her story of a peculiar sexual act with a banana; Lina, the motherly Catholic prostitute with whom Alex and the Monkey had a three-way sexual encounter; Bubbles, the Italian girl with a picture of Jesus over her sink who gave Alex his first, and completely unsuccessful, sexual experience; Kay and Sarah, a pair of very different all-American girls with whom Alex had separate, equally unsuccessful sexual relationships while in college; and finally there is Naomi, a very Jewish liberal with whom Alex is completely unable to be sexual, and who for him (and for the reader) comes to represent Alex's failure to integrate his identity with his desires and, ultimately, his fundamental human truth.

The book's narrative tends to ramble, with stories told in fragments reaching their conclusions only several pages later. Evocative of Alex Portnoy's equally fragmented state of mind, the narrative nevertheless creates a complete picture, a mosaic of tortured desire, regret, frustration and fear (and the occasional glimpse of joy) that ultimately can be seen as portraying not only the life and experience of a unique individual, but the frustrated desire of anyone striving to break free of restriction.